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DealQuest Podcast with Corey Kupfer

Author: Corey Kupfer

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Why do some companies grow by leaps and bounds while others only inch forward? Simple. They embrace Deal-Driven Growth in addition to organic growth! DealQuest is where you learn how to strategize, prepare for, find, and complete deals to grow your company faster.

Listen in as host Corey Kupfer takes you behind the scenes with some of the world’s most fascinating deal-savvy business leaders. This is the one place where they can share openly the secret to deals they have done (or failed to do) and the issues, opportunities, benefits, pitfalls and lessons learned.

Here you learn first-hand all about: Powerful deals that require little capital, mergers, acquisitions, and tuck-ins, Joint ventures, partnerships, and strategic alliances, licensing, raising capital and onboarding key employees, negotiating, structuring, finding, valuing, closing and integrating deals.

Don’t be the one at the table who doesn’t grasp the power of Deal-Driven Growth!
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Just wrapped my second year chairing the EO Deal Exchange Conference, and the lessons were off the charts. Here's what happens when you put hundreds of entrepreneurs in a room focused on one thing: growing through deals. Three insights that stood out: The wisdom is already in the room. We ran deal speed networking sessions where members shared their specific needs (buying companies, seeking JV partners, raising capital). The collective knowledge and connections in that room solved problems in minutes that could take months to crack alone. Stop looking outside your network for every answer. Exit satisfaction is shockingly low. Dave Hirsch shared that only about 13% of entrepreneurs who successfully exit are actually happy afterward. His "Inner Board Meeting" concept helps you identify all the different voices and aspects of your personality that need to be satisfied by any deal you pursue. Powerful framework for avoiding founder depression. Lifestyle business isn't an insult. Silicon Valley prodigy Fallon Fatemi, who co-founded an AI company with Mark Cuban, shared that she'll never raise capital again. Not because capital is bad, but because her priorities have shifted. Build the business and life YOU want, not what others expect.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/kraftheinz• • •FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
85% of founders have regrets about their exits. The research is clear. But here's what surprised me most about this statistic: almost none of them regret leaving money on the table. They regret the clarity work they didn't do beforehand. In my latest conversation with Jodi Hume, an advisor who works exclusively with founders and CEOs navigating acquisitions and exits, we explored what that clarity actually looks like: How to distinguish between what you can compromise on and what will keep you awake at night years later. Why energy management during due diligence directly impacts the quality of your decision-making. The identity piece nobody talks about: who you are after the company is no longer yours. How to protect yourself from making decisions born of depletion rather than strategy. The uncomfortable truth about founder burnout and when an exit might be the right call precisely because you've hit your limit. Jodi's approach is unusual. She's less interested in maximizing valuations than in ensuring founders actually get what they came for—and that they don't regret it afterward. Listen to the full episode if you're even thinking about an exit in the next few years. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jodihume FOR MORE ON JODI HUME:https://www.linkedin.com/in/joditurnerhume/https://atthecore.com/ FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Concentration beats diversification. One stock. That's all Jaden Sterling bought during the 1990s. It tripled, became capital for 125 real estate deals, and eventually funded Sterling Stock Picker, a stock-picking platform now serving 3,000 investors. What most financial advisors don't tell you: diversification is what you do when you don't know what you're doing. When Jaden's clients at Merrill Lynch held 4-6 solid companies, they were pressured to sell and diversify into mutual funds. The math later showed holding those original positions would've beaten all the churn. The path to real wealth isn't about spreading money thin. It's about focused conviction in what you actually understand. I sat down with Jaden to talk about deal structures across real estate, concentrated stock investing, raising capital from customers instead of VCs, and why your relationship with money mirrors your relationship with yourself. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jadensterling FOR MORE ON JADEN STERLING:https://www.sterlingstockpicker.com/jaden_sterling FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
I just had an incredible conversation with Jon Wells on the DealQuest Podcast about a real estate niche that most investors have never even considered. After 25 years in Denver real estate, Jon discovered something remarkable: group homes for mental health and sobriety programs that generate 6%+ cap rates with almost zero landlord responsibilities. Here's what struck me most from our discussion: Jon's "fix and flop" philosophy completely changed my perspective. "My best deals were the ones that didn't sell," he told me. Those failed flips that he couldn't unload? They became his most profitable long-term holdings and led him to this overlooked niche. The economics are compelling. While everyone fights over compressed margins in traditional real estate (Jon watched fix-and-flip profits shrink from 25% to barely 10%), group homes maintain 6-13% cap rates even in high interest rate environments. His mentor has accumulated 1,000 beds. Jon manages 30-40 beds that provide what he calls "a great living." The structure is brilliantly simple. Operators funded by Medicaid and grants handle everything - maintenance, tenants, daily management. Property owners collect rent. It's "as close to a triple net deal as you can do" in residential real estate. The vetting process Jon shared was eye-opening. Drawing from his 1990s experience helping people save properties from foreclosure, he applies rigorous financial analysis to operators. The key: finding those with grant funding, solid track records, and willingness to accept purchase options so they treat the property like their own. What impressed me most was Jon's disciplined approach to avoiding shiny object syndrome. After a syndication advisor told him "I wouldn't touch that with a ten foot pole," he pivoted back to what he knows works - paying off mortgages and creating owner-carry notes for stable, predictable income. The lesson? While everyone chases the same crowded strategies, the best opportunities often hide in markets others don't even know exist. Sometimes the path to financial freedom isn't about following the crowd, but about finding overlooked niches that match your values and expertise. Listen to our full conversation on the DealQuest Podcast where Jon reveals his complete framework for evaluating group home opportunities. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jonwells FOR MORE ON JON WELLS:https://www.linkedin.com/in/jonwellsrealtor/ https://abetterwayrealty.com/  FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Warren Buffett called it one of his biggest investment mistakes.The 2015 Kraft Heinz merger destroyed $63 billion in shareholder value while the broader market doubled.Key lessons for M&A professionals:• Consumer behavior trend analysis is critical for food industry due diligence • Aggressive cost reduction can eliminate innovation capacity in consumer products • Post-merger integration strategies must balance efficiency with brand development • Market research capabilities become essential during rapid cultural shifts • Strategic exit planning requires objective assessment of recovery prospectsThe complete merger failure analysis reveals why sophisticated investors missed consumer preference shifts toward natural foods and how 3G Capital's cost optimization strategy backfired in processed food markets.Essential listening for dealmakers in consumer products industries.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/kraftheinz• • •FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Think great communication in deals is about having the right words or perfect hand gestures? After 35 years of negotiating deals, I can tell you this: all the tactical training in the world won't help if you haven't done the internal work to understand who you are and what you bring to the table. In this episode, Dia Bondi breaks down why your leadership voice matters more than any communication skill. She turned a $30,000 project into over a million dollars by structuring it as a mix of cash and equity. She helped a client maneuver a complex secondary deal by crafting a multi-layered ask that positioned him as an equal partner. And she showed a founder how to create $10 million in value by painting a picture that helped an entire room recognize the moment they were in. Dia shares her six attributes of clutch communicators, including how to:Make strategic asks that create value for everyone (not just get you what you want)Use killer setups that feel natural to your voiceBridge your unique perspective to whatever you're buildingShow up big in big moments even when it feels uncomfortable This conversation reveals why "be authentic" is useless advice and what to focus on instead. Perfect for founders heading into funding rounds, executives negotiating partnerships, or anyone who needs to speak powerfully when stakes are high.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/diabondi• • •FOR MORE ON DIA BONDILinkedIn: https://www.linkedin.com/in/dia-bondi/Company: https://www.diabondi.com/The Book: https://www.asklikeanauctioneer.com/FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
"Every time I get off the phone with you, I feel better... but I don't call because I don't want to pay the billable hour."Alexandria Seydel heard this from clients constantly when she was practicing M&A law. So she made a simple offer: "What about once a month you buy me lunch and we go for 90 minutes and you get my brain."Those lunch conversations changed everything. Alexandria realized she was more energized talking business strategy than drafting legal documents. Now as founder of Ripples Edge Advisors, she helps business owners prepare for exits before they're forced to sell.Most owners think exit planning means getting financials in order and hoping for the best. Alexandria starts differently. She has clients close their eyes and picture life five years after selling: What does your typical day look like? Who are you spending time with? What gives you purpose?Those answers determine whether you should target private equity (focused on returns) or strategic buyers (who care about legacy and team). The visioning exercise prevents what Alexandria sees constantly: post-exit depression, even among sellers who make life-changing money.Right now she's watching clients in tech-adjacent industries get multiple serious offers in the same week. Legal tech, agricultural tech, climate tech - traditional industries adding technology are hot. But success isn't just about timing the market."If you were to go to Bali for three weeks, would your business run without you?" That's Alexandria's test for exit readiness. Most entrepreneurs think they're prepared until they actually try stepping away.In our conversation, Alexandria breaks down her exit readiness assessment, explains why the visioning exercise matters more than most tactical work, and shares what's driving current M&A activity in her clients' industries.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/alexandriaseydel• • •FOR MORE ON ALEXANDRIA SEYDEL LinkedIn: https://www.linkedin.com/in/alexandria-seydel/Company: https://www.linkedin.com/company/ripples-edge-advisors/Website: https://www.ripplesedgeadvisors.com/FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Think investors who don't re-up for your next round are doing you a favor?Not the case!Most entrepreneurs see this as rejection. But here's what Sahil Patel discovered after 11 years building and selling ER Express: Sometimes the BEST thing that can happen is getting misaligned investors out of your cap table.His family office investors knew service businesses. But SaaS? Different game entirely."The way you look at a SaaS business, you really have to look at unit economics. If you just look at the whole cost, it looks terrible."The result? A year of treading water while growth stalled.But here's where it gets interesting: Those same investors offered him a management buyout with seller financing. NON-RECOURSE.Eight quarters of consecutive growth followed.We'll dive deep into this (and so much more) in this episode of the DealQuest Podcast! How to identify when investor misalignment is killing your business Why timing is the entrepreneur's biggest enemy (not money) The crisis pivot that doubled his total addressable market Building performance-based business models that guarantee results And much more Whether you're navigating complex investor relationships or building systems for sustainable growth, this conversation provides frameworks every business leader needs.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/sahilpatel• • • FOR MORE ON SAHIL PATELhttps://www.linkedin.com/in/sahilanamipatel/https://www.spiralyze.com/ FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
JP Morgan's latest M&A report reveals something fascinating: despite ongoing uncertainty, global deal volumes hit $2.2 trillion (up 27% year-over-year).Here's what caught my attention: - Mega deals increased 57% because bigger players can thrive when smaller competitors freeze up. - Cross-border activity actually grew 24% despite rising protectionism as companies use M&A to position around trade uncertainties rather than avoid them. - And get this - AI infrastructure needs will drive $1 trillion in spending over the next 5 years, with data center capacity needing to increase 100-fold.Technology M&A surged 42%, financial services up 56%, and even media jumped 51% as consolidation becomes a survival strategy.The bottom line? Uncertainty isn't going away, but markets remain remarkably resilient. Smart deal-makers are learning to operate effectively in permanently uncertain conditions rather than waiting for clarity that may never come.Listen to my full breakdown on this solo DealQuest episode.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/JPMorgan2025• • •FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Ever wonder how great dealmakers got their start?Some began with childhood lemonade stands. Others learned through necessity when family circumstances required quick business education. A few discovered their talents through door-to-door sales or car flipping as teenagers.But here's what's fascinating: every successful dealmaker has an origin story that reveals the early development of skills that would later drive millions in transactions.In this best of compilation from the DealQuest Podcast, you'll hear from over a dozen successful business leaders sharing their very first deals - from Thomas Samuelson negotiating his way out of Philadelphia to Sunny Vanderbeck subcontracting lawn care in elementary school.What you'll discover: How childhood businesses teach fundamental negotiation principles Why early sales experiences translate directly to deal success The common patterns that predict future dealmaking ability How adversity often accelerates business skill development And much more Whether you're developing your own deal skills or helping others recognize their potential, these stories provide insights into how business instincts develop and grow. • • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/originstories• • •FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Most people think private equity means gutting companies and squeezing margins. Neal Cobb is proving them wrong.After raising over $20 million and scaling his delivery startup to 100,000 drivers before selling to 7-Eleven, Neal could have retired. Instead, he's building something that challenges everything we think we know about private equity.At Equity X, they're acquiring legacy businesses and turning them into employee-owned enterprises. No quick flips. No cultural destruction. Just long-term value creation where employees actually benefit from the success they help create.In this DealQuest conversation, Neal shares how he went from running dice games in high school to building a white-label delivery empire to reimagining what private equity can be. His insights on partnerships, timing deals, and betting on people over ideas will change how you think about business growth.Neal's approach reveals what happens when you prioritize people and culture alongside profits.This is a perfect listen for business leaders exploring acquisition strategies and sustainable growth models.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/nealcobb• • • FOR MORE ON NEAL COBBhttps://www.linkedin.com/in/neal-cobb-4a4084179/www.equityx.co FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
 Eighty percent of business owners have eighty percent of their net worth locked in their business.But only twenty percent of businesses survive to see their tenth birthday.This conversation will change how you think about building enterprise value forever.Scott Beebe didn't just build a successful consulting practice...He proved that the secret to enterprise value isn't your product, your market, or your marketing.Scott is the founder of Business on Purpose and certified exit planning advisor who has helped hundreds of business owners liberate themselves from chaos while building sellable assets.In this DealQuest Podcast episode, I sat down with Scott to uncover the real drivers of enterprise value and why most businesses fail the ultimate test.In our conversation, we explored: The eighty percent rule that destroys most businesses Why your product isn't actually your product The enterprise value litmus test every owner should know How to break free from "hero complex" that kills scalability The five meeting types that build culture and systems Cash domination strategies that put owners in control And much more!Whether you're planning an exit in two to three years, building for long-term growth, or struggling with operational chaos, this conversation provides actionable frameworks for immediate implementation.  • • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/scottbeebe• • • FOR MORE ON SCOTT BEEBECompany: https://www.businessonpurpose.com Assessment Tool: https://www.businessonpurpose.com/healthy Books: "Let Your Business Burn" and "The Chaos Free Contractor" FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Most business leaders believe they need significant capital to pursue growth deals.This assumption limits their strategic options.The reality is that dozens of deal structures are available to businesses of every size, yet most entrepreneurs only explore a fraction of what's possible.From acqui-hires that appear to be acquisitions but are actually strategic hiring initiatives, to licensing agreements that generate ongoing revenue, to joint ventures that create value for all parties involved.This episode of the DealQuest Podcast explores the full spectrum of deal opportunities:• The crucial distinction between mergers and acquisitions and why it matters for your strategy • How to structure transactions with zero upfront capital requirements • Why licensing represents the most underutilized revenue opportunity for many businesses • Employee retention strategies that function as internal deals • And much moreEssential listening for business owners seeking to understand their complete range of strategic growth options.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/languageofdeals• • •FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Hikari Senju did something different. While everyone else was chasing VCs, he built Omneky to millions in revenue first. After seeing AI generate art at MIT, this Harvard CS grad knew the future. But when investors didn't bite in 2018 ("AI is vaporware," "advertising is too competitive"), he didn't give up. He bootstrapped. Two years. Living hand-to-mouth. Building real revenue. His philosophy: "Build a company that deserves capital." The result? When he finally raised money, he had leverage. He was selecting partners, not begging for checks. Three insights from our conversation that reinforce critical deal principles: Strategic exits: He took less money from his first sale to learn inside a funded startup. That buyer became his first investor in Omneky. The deserve capital test: Growing 3x with strong margins? Investment should be obvious. If not, keep building. Infinite game thinking: Every deal starts a relationship. Your vendor today might be your investor tomorrow. From selling art to grandma at 7 to serving Fortune 100s with AI. • • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/hikarisenju• • • FOR MORE ON HIKARI SENJULinkedIn: https://www.linkedin.com/in/hisenju/Omneky: www.omneky.com FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Most real estate developers think they need institutional investors or private equity to scale their projects.Ryan Andrews proved you can raise millions locally while building stronger community connections.Here's what makes this approach powerful:His $8 million fund is 80% local investors who show up to city council meetings advocating for his projects.These aren't just silent money partners.They're community champions.When your investors live in the community, they care about getting it right."We've had investors showing up at city council meetings, advocating for the projects, and giving public testimony. And like, it gives you a really different kind of investor." - Ryan AndrewsWe'll dive deep into this (and so much more) in this episode of the DealQuest Podcast:• Systematic approaches to local capital raising • Building investor relationships in small communities • Scaling through developer partnerships nationwide • Creating attainable housing that communities actually want Perfect for: Real estate developers, entrepreneurs seeking community-driven growth strategies, and business leaders looking for alternatives to institutional capital. • • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/ryanandrew• • • FOR MORE ON RYAN ANDREWRyan Andrew's LinkedIn Hiatus Homes Email: ryan@hiatushomes.com FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Most business leaders think scaling requires massive capital investment.But what if I told you companies are scaling from 7 to 9 figures through strategic partnerships instead?That's exactly what this business scaling expert has been doing for the past decade.Through systematic partnership frameworks and strategic deal-making.And guess what? His approach started when he was just 13 years old, creating partnership deals to expand beyond his local market."Why am I limiting myself to my school? Why don't I actually find people in other schools who I can work with?"That one systematic question became the foundation for scaling multiple companies to nine-figure revenue.Here's what surprised me: This expert has customers in Europe and Africa but has never done business development in those markets.How? Strategic partnership systems that systematically refer qualified customers.We'll dive deep into this (and so much more) in this episode of the DealQuest Podcast! Proven frameworks for partnering with larger firms even when you're small Why white-labeling strategies can accelerate your brand building Partnership structures that create sustainable long-term growth Strategic decision-making frameworks for equity vs. cash deals If you're ready to scale your business beyond organic growth using proven partnership frameworks, this conversation provides a systematic blueprint. • • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/nahedkhairallah• • • FOR MORE ON NAHED KHAIRALLAHhttps://www.linkedin.com/in/khairallahnahed/https://organizedchaos.fyi Email: hello@organizedchaos.fyi FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Most entrepreneurs think M&A and capital raising are the only "real" deals.They're missing 90% of the opportunities.In this DealQuest solo episode, I break down the full spectrum of deal types that can solve virtually any business challenge: Strategic partnerships and alliances Technology licensing and transfer deals Operational and supply chain partnerships Asset deals and real estate transactions Financial restructuring options Emerging digital economy deals The truth? There's a deal for virtually every business problem.You just need to know what's possible.Perfect for: Business leaders, entrepreneurs, and anyone looking to grow through strategic partnerships rather than traditional funding. • • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/dealforthat• • •FOR MORE ON COREY KUPFER:https://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Most entrepreneurs think raising VC money means they've "made it."But Tom Dillon learned something different during his years in investment banking and running a PE-backed company.After analyzing countless deals and experiencing the pressure firsthand, he discovered that VC money comes with a specific expectation: IPO-level returns."For a lot of VCs, they kinda look at things in terms of roulette table. They really need one of those to hit big."The problem? Most successful businesses exit through M&A, not IPOs.So if you're building a profitable company that could sell for $20-50M in a few years, VC funding might actually work against you.Tom now helps founders as a fractional CFO, matching funding strategies to realistic business goals rather than chasing the biggest check.In this episode, we explore:• Why thinking multiple rounds ahead is crucial for any capital raise • Alternative funding sources that align with M&A exits • The growing trend of buying your first business instead of starting one • How to set realistic valuation expectations • The mindset shifts that separate successful founders from those who strugglePerfect for entrepreneurs evaluating funding options and business owners planning exit strategies.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/tomdillon• • • FOR MORE ON TOM DILLONhttps://www.linkedin.com/in/tomdilloncfa/ https://fracfinance.com/ FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Georgi Feidler shared some incredible stats with me... Over 50% of small businesses are owned by Baby Boomers. 60% of those have zero succession plan.That's billions in wealth transfer happening right now and most of it is going to be messy.Georgi has spent 20+ years helping founders navigate this transition. Her approach isn't just about finding buyers - it's about building businesses that can actually survive without their founders.The brother/sister case study she shared shows how creative structuring can cut transition time from years to months.Perfect for business owners planning exits or anyone working with Boomer-owned businesses.Georgi is the founder of Hire, Train, Aspire and a seasoned leader with 20+ years of experience who's helped scale companies from small teams to organizations with over 68,000 employees through IPOs, mergers, acquisitions, and capital raises.In this episode, she breaks down how to overcome the "tribal knowledge problem," build confidence in your team to run without you, and create succession plans that work for both internal and external transitions.We talked about business exits, succession planning, and freedom, the kind that comes from building something bigger than yourself.So if you're a business owner thinking about your exit strategy or a Baby Boomer founder wondering how to preserve your legacy, you'll want to hit play on this one.• • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/georgifeidler• • • FOR MORE ON GEORGI FEIDLERGeorgi Feidler's LinkedInHire, Train, Aspire FOR MORE ON COREY KUPFERCorey Kupfer's LinkedInCorey Kupfer's Website Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Attention entrepreneurs: If you think working 80+ hour weeks makes your business more valuable... the data says otherwise.This conversation will change how you think about business building forever.James Brown didn't just sell his business for multiple cash offers he proved that less owner involvement equals higher business value.James is the founder of BizTech Guru, a business consultant who transformed his own accommodation business over many years from requiring 120-hour work weeks to just 30 minutes of monthly involvement. After surviving multiple economic challenges including the Global Financial Crisis and COVID-19, he eventually sold the business with 7 offers, 3 of which were cash.In this episode, he exposes the shocking truth about why 80% of businesses aren't sellable, reveals his exact automation playbook, and shares the mindset shifts that create truly passive income.We talked about business automation, but not the tech-heavy complicated kind.We talked about remote team management, but not the micromanagement nightmare kind.And we talked about exit preparation, the kind that actually increases your quality of life WHILE building value.This completely changed my perspective on what makes businesses valuable.Perfect for: SaaS founders, service business owners, e-commerce entrepreneurs, and anyone building for eventual exit. • • •FOR MORE ON THIS EPISODE:https://www.coreykupfer.com/blog/jamesbrown• • • FOR MORE ON JAMES BROWNJames Brown's LinkedIn BizTech Guru WebsiteFOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/http://coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
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